2-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-ol → 2-[3-(4-Fluoro-3-(pyrazol-1-yl)phenyl)imidazo[1,2-alpha]pyrimidin-7-yl]propan-2-ol

HRID 2184061Notes

Reaction equation

HRID 2184061 reaction equation
CC1(C)COB([C:8]2[CH:9]=[CH:10][C:11]([F:19])=[C:12]([N:14]3[CH:18]=[CH:17][CH:16]=[N:15]3)[CH:13]=2)OC1.Br[C:22]1[N:26]2[CH:27]=[CH:28][C:29]([C:31]([OH:34])([CH3:33])[CH3:32])=[N:30][C:25]2=[N:24][CH:23]=1>>[F:19][C:11]1[CH:10]=[CH:9][C:8]([C:22]2[N:26]3[CH:27]=[CH:28][C:29]([C:31]([OH:34])([CH3:32])[CH3:33])=[N:30][C:25]3=[N:24][CH:23]=2)=[CH:13][C:12]=1[N:14]1[CH:18]=[CH:17][CH:16]=[N:15]1

Participants

3

Reactant 2

HCID 112422822-(3-Bromoimidazo[1,2-a]pyrimidin-7-yl)propan-2-olHCID 223294941-[5-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-2-fluorophenyl]-1H-pyrazole

Product 1

HCID 697078212-[3-(4-Fluoro-3-(pyrazol-1-yl)phenyl)imidazo[1,2-alpha]pyrimidin-7-yl]propan-2-ol

Procedure

1-[5-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-2-fluorophenyl]-1H-pyrazole (300 mg, 1.0 mmol) was coupled to 2-(3-bromoimidazo[1,2-α]pyrimidin-7-yl)propan-2-ol (256 mg, 1.0 mmol) using the method in Example 1. Purification by chromatography on silica gel eluting with dichloromethane containing 5% methanol then trituration with diethyl ether gave 2-[3-(4-fluoro-3-(pyrazol-1-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl]propan-2-ol as a white solid: δH (400 MHz, CDCl3) 1.63 (6H, s), 4.40 (1H, br s), 6.54 (1H, t, J 2), 7.09 (1H, d, J 7), 7.40-7.44 (2H, m), 7.77 (1H, d, J 2), 7.89 (1H, s), 8.13 (1H, t, J 3), 8.16-8.19 (1H, m), 8.65 (1H, d, J 7); m/z (ES+) 338 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane containing 5% methanol

Sources & evidence

ORD record
ord-971ba1c5ac75466a883ea40a61d1c468
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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